Azodyestuffs and process of making same



" Patented June 1, 1926.

ARTHUR ZITSGHER, OF OFFENBACH-ON-THE-MAIN, GERMANY, ASSIGNOR TO THE CORPORATION OF CEEMISCHE FABRIK G ON-IHE-MAIIN', GERMANY.

RIESHEIM-ELEKTRON, OF FRANKFURT- AZODYESTUFFS AND PROOESS OF MAKING SAME.

Io Drawing. Application filed November 30, 1923, Serial No. 677,878; and in Germany January 12,- 1928.

My invention relates to valuable azohydroxynaphthoyl) 4.4. diamino 3.3- dyestufis, whichmay be obtained by com- 'lialkyloxy-diaryls of the general formula: 6

bining any diazocompound with his (2.3-

wherein R and R mean the same or diifer ent monovalent substituents.

The especial value of my invention resides in the fact that it yields dyestufis of a '10 more pronounced brown shade than other dyestuffs, derived from the arylids of 2.3- hydroxynaphthoic acid. The dyestuffs are when 15 soluble in water, soluble in, sulfuric acid to a red to reddish violet solution, yielding CHgO dry brownish red, brown to deep reddish'brown powders, in-.

dins,

aminoazobodies, diaminobases and others.

naphthylamins, aminoanthraquinones,

The bis-(2.3-hydroxynaphthoyl) -4.4-diamino- 3.3'- dialkyloxydiaryls, not known hitherto, can be obtained by heating 4.4'- diamino 3.3 dialkyloxydiaryls togetherwith 2.3-hydroxynaphthoic acid.

Thefollowing example illustrates the in vention.

The cottonyarn, Well boiled and dried, is 40 impregnated with a solution of gr. v 1sof 2.3-hydroxynaphthoyl) -dianisidin,

cc. of caustic soda solution of 34 B. and cc. of Turkey red oil per liter well wrung out and developed without ina drying 4c diazosolution, containing 3.3 of 2.5-

dichloroanilin per liter, to whi sodium acetate has been added, whereupon the yarn is rinsed and soaped while boiling.

In of a dyestufi' thus formula this manner deep orange-brown shades very good fastness are obtained. The produced probably has the The new dyestufis can also be produced by using the nitrosa nriin salts of the correby; printing a. diazosolution .upon padded sponding bases.

goods-according to the usual method, also ith other diazocoinpounds'and also for Q; L -1, ae7,oeo

example with bis-(2.3- ydroxinephthoyh- The following table gives the shades of a diphenetidin the process may e conducted number of dyestuffs, prepared according to 5 slmllarly. the present process Diazocompound of- Combined with- Shades. Diazocompound of Combined with Shades.

Meta-chioroanilin Bis- (2.3 h {d r o x y- Orange-brown. a'aminoanthraquinone Bis-(2.341 y d r o x y Reddish brown.

naphthoy )-diamszdlgghthoyh-dianlsi- 1 n. 2.5 dichloroanilin do. (example) Deep orange-brown. Meta-aminoazotoluene. d0 Deep reddish brown. 3.5-dichloroanilim. Do. Benzidin Pace-brown. I 4-chloro-L2-toluidin Brownish red. 0rtho-telidin Maroon. chl0ro-1.2-toluidin Do. Dinnisidin I do Purplish brown. 4-chloro-L3-toluidin Reddish brown. Meta-chloroanilin. Bis-(2.3 b y d r o x y- Reddish brown. 4-chloro-l.2-anisidin. Brownish dark red. naphthoyD-diphene- 4-nitro-L2-toluidin... Orange-brown. tidin.

" 5-mtro-L2-to1uidin .do Reddish dark brown. 2.5-dichloroanilin Deep orange-brown.

3-nitro-L4- Reddish brown. 3.5-diehloroauilin Reddish brown. 4-nitro-L2-anisidin -.do Do. 5-nitro-l.2-toluidin Do 5-nitro-1.2-an.isidin Dark reddish brown. 3-nitro-L4-toluidin-.. Brownish red. 6-nitr0-1.3-anisidin Deep brown. 4-nitro-L2-am'si n Reddish brown. 4-chIoro-2-nitroanilin- Reddish brown. 5-nitro-1.2-anisidin Brownish dark red 5-chloro-2-nitroanilln- Brown. 4-chloro-2-nitroanilin- Dark reddish brown. 2-ch1oro-4-nitroaniiin. Dark brown. 5-chloro'2-nitr oanililn. 0range-brown. 3-chloro4-nitroani1in- Brown. Z-chloro--nitroanilin Brown. 3.5-dinitroanilin. Do. 3-ch1oro-4-nitroani1in. o. A-nitro-anthram'lic acid Reddish brown. 3.5-dinitroani1in Orange-brown.

methyl ester. a-aminoanthraquinone Reddish brown. G-nitro-S-aminobenzoic Do. Meta-aminoazotoluene Deep reddish brown.

acid ethyl ester.

. When a diazocompound of meta-aminodroxynaphthoyl)-dianisidin, the resulting w ezotoluene is combined with bis-(2.3-hydyestufi probably has the formula: Qua on I ll ll Qua, OE Q i ll OH E0 OO-NH NE-OO CH1 CH1 When a diazoeompound of benzidin is dienisidin, the resulting dyestufi prohably combined with b1s-(2.3-hydroxynaphthoyl)- has the formula:

5 Now what I claim and desire'to secure by i When a diazocompound of a-aminoam thraquinone is combined with bis-(2.3-hydroxynaphthoyl)-diphenetidin, the resulting dyestufi probably has the formula:

Letters Patentv is the following Aryl o o-mr g; pai -o.

1. new articles the azodyestuflis, having probably the general. formula;

Aryl

stufl's giving, when produced {an the fiber, brownish red, orange-brown to deep brown shades of a very good fastness. on cotton.

2. A process of making. azodyestufls consisting in combinin any diazocompound with a his (2.3-hy roxynaphthoyl)-4.4'diamino-3.3'-dialkyloxydiaryl having probablp the general formula:

i a NH 00 wherein R and B mean the same or difi'erent ing developed on the fiber of the material.

monovalent substituents.

3. Materials dyed with the new azod estuffs according to claim 1, said dyestufls ewhich are when dry brownish red,

deep reddish brown to brown powders, insoluble in water and soluble in sulfuric acid to a red 4. As new articles the azodyestufis, having probably the general formula:

duction with starinous chlorlde two 1110 ocular proportions of an aromatic amin' and one droxy-3 -naphthoyl) -dianisidin,

molecular proportion of bis-(1-amino-2-hysaid dyestufis giving, when produced on the cotton fiber, brownish red, orange-brown to deep brown shades of a very good fastness.

5. A process of making azodyestuffs consisting in combining any diazocompound with bis- (2.3-hydroxynaphthoyl) -dianisidin, having probably the formula:

6. Materials dyed with the new. azodyestufis according to claim 4, said dyestuffs being developed on the fiber of the material.

7. As a new article the azodyestufi, having probably the formula:

it i

- on a no 0 0-NHQQNH-O o i i cm on,

- molecular proportions of 2.5-dichloroanilin and one molecular proportion of bis-(l-amino-2-hydroxy-3-naphthoyl)-dianisidin, said dyestufl' giving, when produced on the cotton fiber, deeply orange-brown shades of a very good fastness.

8. process of making an azodyestufl ARTHUR ZITSOHER. 

